benzatropine Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
atropine derivatives 333 86-13-5

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • cogentin
  • benztropine mesilate
  • benzatropine
  • benztropine
  • tropine benzohydryl ether
  • benztropine mesylate
A centrally active muscarinic antagonist that has been used in the symptomatic treatment of PARKINSON DISEASE. Benztropine also inhibits the uptake of dopamine.
  • Molecular weight: 307.44
  • Formula: C21H25NO
  • CLOGP: 3.52
  • LIPINSKI: 0
  • HAC: 2
  • HDO: 0
  • TPSA: 12.47
  • ALOGS: -5.41
  • ROTB: 4

  • Status: OFP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
2 mg O
2 mg P

ADMET properties:

PropertyValueReference
MRTD (Maximum Recommended Therapeutic Daily Dose) 0.21 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BDDCS (Biopharmaceutical Drug Disposition Classification System) 1 Hosey CM, Chan R, Benet LZ
BA (Bioavailability) 29 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H

Approvals:

DateAgencyCompanyOrphan
March 5, 1954 FDA

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Granulocytopenia 337.77 17.60 95 8886 5178 46671903
Completed suicide 254.82 17.60 216 8765 145704 46531377
Tardive dyskinesia 164.97 17.60 60 8921 7483 46669598
Schizophrenia 157.52 17.60 60 8921 8508 46668573
Psychotic disorder 148.89 17.60 77 8904 22544 46654537
Neuroleptic malignant syndrome 116.19 17.60 52 8929 11070 46666011
Toxicity to various agents 110.25 17.60 167 8814 211599 46465482
Extrapyramidal disorder 109.22 17.60 50 8931 11218 46665863
Paranoia 105.79 17.60 48 8933 10549 46666532
Hallucination, auditory 101.96 17.60 47 8934 10709 46666372
Sedation 78.41 17.60 51 8930 22859 46654222
Dystonia 70.25 17.60 37 8944 11220 46665861
Muscle rigidity 65.76 17.60 34 8947 9927 46667154
Agitation 61.53 17.60 64 8917 55351 46621730
Blood prolactin increased 58.51 17.60 22 8959 3005 46674076
Catatonia 53.87 17.60 22 8959 3740 46673341
Schizoaffective disorder 53.14 17.60 17 8964 1435 46675646
Ileus paralytic 50.92 17.60 22 8959 4301 46672780
Clonus 48.83 17.60 21 8960 4059 46673022
Tremor 48.74 17.60 83 8898 115556 46561525
Suicidal ideation 46.89 17.60 56 8925 56326 46620755
Dyskinesia 46.52 17.60 41 8940 28884 46648197
Aggression 44.30 17.60 36 8945 22708 46654373
Hyperreflexia 43.74 17.60 21 8960 5233 46671848
Drooling 43.34 17.60 18 8963 3191 46673890
Oculogyric crisis 43.34 17.60 14 8967 1219 46675862
Akathisia 41.55 17.60 23 8958 7691 46669390
Myocarditis 41.48 17.60 23 8958 7716 46669365
Leukopenia 41.35 17.60 58 8923 68285 46608796
Delusion 40.97 17.60 26 8955 11162 46665919
Galactorrhoea 40.43 17.60 18 8963 3779 46673302
Salivary hypersecretion 36.88 17.60 20 8961 6425 46670656
Abnormal behaviour 36.18 17.60 31 8950 21027 46656054
Treatment noncompliance 36.00 17.60 36 8945 29695 46647386
Amaurosis 35.85 17.60 10 8971 526 46676555
Haemoglobin urine 33.03 17.60 7 8974 113 46676968
Confusional state 31.31 17.60 84 8897 159808 46517273
Hallucination 31.11 17.60 43 8938 49908 46627173
Mydriasis 30.12 17.60 21 8960 10532 46666549
Cardiac arrest 29.35 17.60 58 8923 90341 46586740
Parkinsonism 27.93 17.60 18 8963 7930 46669151
Torsade de pointes 27.46 17.60 21 8960 12133 46664948
Toxic encephalopathy 27.00 17.60 15 8966 5047 46672034
Amenorrhoea 26.08 17.60 18 8963 8877 46668204
Hyperprolactinaemia 25.26 17.60 12 8969 2920 46674161
Diabetes mellitus 25.22 17.60 39 8942 50026 46627055
Encephalitis autoimmune 24.78 17.60 9 8972 1115 46675966
Red blood cells urine 24.06 17.60 7 8974 429 46676652
Lipids decreased 24.00 17.60 4 8977 15 46677066
Arthralgia 23.95 17.60 21 8960 364582 46312499
Eosinophil count abnormal 23.52 17.60 7 8974 464 46676617
Weight increased 23.24 17.60 77 8904 164396 46512685
Electrocardiogram QT prolonged 23.13 17.60 38 8943 51287 46625794
Dysarthria 22.92 17.60 32 8949 37466 46639615
Suspected suicide 22.67 17.60 13 8968 4648 46672433
Schizoaffective disorder bipolar type 22.08 17.60 5 8976 111 46676970
Joint swelling 21.90 17.60 3 8978 166070 46511011
Cognitive disorder 21.84 17.60 31 8950 36852 46640229
Facial paralysis 21.73 17.60 19 8962 13231 46663850
Diarrhoea 21.08 17.60 48 8933 559554 46117527
Mania 20.76 17.60 17 8964 10829 46666252
Restlessness 20.62 17.60 25 8956 25499 46651582
Cardio-respiratory arrest 20.13 17.60 39 8942 59830 46617251
Mental disorder 19.83 17.60 23 8958 22402 46654679
Bipolar disorder 19.82 17.60 14 8967 7163 46669918
Areflexia 19.03 17.60 10 8971 3013 46674068
Device leakage 18.48 17.60 12 8969 5353 46671728
Metabolic disorder 17.99 17.60 11 8970 4421 46672660

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Granulocytopenia 532.51 17.68 161 10493 6065 29935759
Completed suicide 198.99 17.68 209 10445 99283 29842541
Neuroleptic malignant syndrome 168.49 17.68 92 10562 16203 29925621
Tardive dyskinesia 152.39 17.68 60 10594 4997 29936827
Myocarditis 148.26 17.68 72 10582 9939 29931885
Psychotic disorder 147.27 17.68 93 10561 21422 29920402
Extrapyramidal disorder 134.98 17.68 69 10585 10624 29931200
Schizophrenia 124.79 17.68 62 10592 8986 29932838
Toxicity to various agents 120.49 17.68 221 10433 176962 29764862
Agitation 97.96 17.68 108 10546 53965 29887859
Hallucination, auditory 92.18 17.68 52 10602 9737 29932087
Dystonia 84.44 17.68 49 10605 9678 29932146
Akathisia 77.11 17.68 39 10615 5865 29935959
Drooling 71.15 17.68 30 10624 2975 29938849
Tremor 69.61 17.68 108 10546 75255 29866569
Device leakage 62.08 17.68 29 10625 3665 29938159
Galactorrhoea 61.61 17.68 16 10638 339 29941485
Sedation 61.28 17.68 49 10605 16324 29925500
Hyperprolactinaemia 61.26 17.68 21 10633 1179 29940645
Leukopenia 61.20 17.68 87 10567 56072 29885752
Syringe issue 56.05 17.68 25 10629 2840 29938984
Paranoia 54.98 17.68 38 10616 10150 29931674
Abnormal behaviour 54.89 17.68 56 10598 25567 29916257
Muscle rigidity 54.74 17.68 38 10616 10223 29931601
Schizoaffective disorder 51.98 17.68 18 10636 1042 29940782
Treatment noncompliance 51.94 17.68 54 10600 25199 29916625
Product dose omission issue 49.50 17.68 104 10550 91527 29850297
Drug abuse 47.68 17.68 96 10558 81976 29859848
Aggression 47.49 17.68 62 10592 36845 29904979
Dystonic tremor 44.45 17.68 10 10644 112 29941712
Priapism 44.11 17.68 25 10629 4718 29937106
Inappropriate schedule of product administration 43.92 17.68 62 10592 39666 29902158
Antipsychotic drug level increased 41.59 17.68 21 10633 3145 29938679
Catatonia 40.50 17.68 23 10631 4357 29937467
Cogwheel rigidity 39.63 17.68 15 10639 1121 29940703
Drug interaction 38.96 17.68 157 10497 199411 29742413
Parkinsonism 38.95 17.68 27 10627 7242 29934582
Restlessness 37.21 17.68 43 10611 22556 29919268
Mental status changes 35.39 17.68 54 10600 37025 29904799
Delusion 34.79 17.68 31 10623 11958 29929866
Drug level increased 33.76 17.68 37 10617 18317 29923507
Dyskinesia 33.38 17.68 40 10614 21794 29920030
Agranulocytosis 33.22 17.68 40 10614 21902 29919922
Anticholinergic syndrome 32.85 17.68 12 10642 812 29941012
Suicidal ideation 32.23 17.68 51 10603 36063 29905761
Blood prolactin increased 29.72 17.68 13 10641 1409 29940415
Lethargy 28.85 17.68 51 10603 39468 29902356
Eosinophilic pleural effusion 28.82 17.68 8 10646 220 29941604
Homicidal ideation 28.49 17.68 15 10639 2448 29939376
Needle issue 27.27 17.68 17 10637 3815 29938009
Mania 27.22 17.68 24 10630 9130 29932694
Oculogyric crisis 26.90 17.68 12 10642 1363 29940461
Weight increased 26.31 17.68 72 10582 74841 29866983
Musculoskeletal stiffness 25.79 17.68 46 10608 35835 29905989
Device malfunction 25.60 17.68 22 10632 8089 29933735
Blood triglycerides increased 25.33 17.68 28 10626 13989 29927835
Antipsychotic drug level decreased 25.09 17.68 10 10644 858 29940966
Febrile neutropenia 25.01 17.68 4 10650 106689 29835135
Bipolar disorder 25.00 17.68 16 10638 3760 29938064
Overdose 24.75 17.68 76 10578 84261 29857563
Sinus tachycardia 24.68 17.68 29 10625 15475 29926349
Delirium 24.12 17.68 48 10606 40583 29901241
Diarrhoea 24.07 17.68 52 10602 334051 29607773
Haemophagocytic lymphohistiocytosis 23.92 17.68 23 10631 9768 29932056
Type 2 diabetes mellitus 22.55 17.68 26 10628 13596 29928228
Blood creatine phosphokinase increased 21.61 17.68 48 10606 43800 29898024
Gynaecomastia 21.13 17.68 20 10634 8331 29933493
Blood pH decreased 21.08 17.68 12 10642 2283 29939541
Salivary hypersecretion 20.84 17.68 19 10635 7547 29934277
Globulins decreased 20.48 17.68 6 10648 201 29941623
Disease progression 18.70 17.68 3 10651 79871 29861953
Psychiatric decompensation 18.09 17.68 9 10645 1306 29940518

Pharmacologic Action:

SourceCodeDescription
ATC N04AC01 NERVOUS SYSTEM
ANTI-PARKINSON DRUGS
ANTICHOLINERGIC AGENTS
Ethers of tropine or tropine derivatives
FDA MoA N0000000207 Histamine Receptor Antagonists
FDA MoA N0000175370 Cholinergic Antagonists
FDA EPC N0000175574 Anticholinergic
FDA EPC N0000175750 Antihistamine
CHEBI has role CHEBI:48407 antiparkinson agent
CHEBI has role CHEBI:48876 antimuskarinika
CHEBI has role CHEBI:50370 parasympatholytics
CHEBI has role CHEBI:66956 antidyskinetic drugs
CHEBI has role CHEBI:146270 oneirogens
CHEBI has role CHEBI:149553 anti-coronaviral agents
MeSH PA D018726 Anti-Dyskinesia Agents
MeSH PA D000978 Antiparkinson Agents
MeSH PA D002491 Central Nervous System Agents
MeSH PA D018678 Cholinergic Agents
MeSH PA D018680 Cholinergic Antagonists
MeSH PA D015259 Dopamine Agents
MeSH PA D018765 Dopamine Uptake Inhibitors
MeSH PA D049990 Membrane Transport Modulators
MeSH PA D018727 Muscarinic Antagonists
MeSH PA D018377 Neurotransmitter Agents
MeSH PA D014179 Neurotransmitter Uptake Inhibitors
MeSH PA D010276 Parasympatholytics
MeSH PA D018373 Peripheral Nervous System Agents

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Postencephalitic parkinsonism indication 19972008 DOID:14332
Parkinsonism indication 32798002
Parkinson's disease indication 49049000 DOID:14330
Extrapyramidal disease indication 76349003
Arteriosclerotic Parkinsonism indication
Urinary tract obstruction contraindication 7163005 DOID:5200
Chronic obstructive lung disease contraindication 13645005 DOID:3083
Severe chronic ulcerative colitis contraindication 14311001
Disorder of autonomic nervous system contraindication 15241006
Toxic megacolon contraindication 28536002 DOID:1770
Atony of colon contraindication 29479008
Shigellosis contraindication 36188001
Hypertensive disorder contraindication 38341003 DOID:10763
Conduction disorder of the heart contraindication 44808001
Low blood pressure contraindication 45007003
Achalasia of esophagus contraindication 45564002 DOID:9164
Chronic heart failure contraindication 48447003
Dysuria contraindication 49650001
Paralytic ileus contraindication 55525008 DOID:8442
Ulcerative colitis contraindication 64766004 DOID:8577
Hiatal hernia contraindication 84089009 DOID:12642
Open-angle glaucoma contraindication 84494001 DOID:1067
Kidney disease contraindication 90708001 DOID:557
Thyrotoxicosis contraindication 90739004 DOID:7997
Myasthenia gravis contraindication 91637004 DOID:437
Tardive dyskinesia contraindication 102449007
Dysentery contraindication 111939009
Gastrointestinal obstruction contraindication 126765001
Bleeding contraindication 131148009
Gastroesophageal reflux disease contraindication 235595009 DOID:8534
Disease of liver contraindication 235856003 DOID:409
Benign prostatic hyperplasia contraindication 266569009
Retention of urine contraindication 267064002
Fever contraindication 386661006
Angle-closure glaucoma contraindication 392291006 DOID:13550
Pseudomembranous enterocolitis contraindication 397683000
Gastric ulcer contraindication 397825006 DOID:10808
Disorder of coronary artery contraindication 414024009

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 9.86 Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Muscarinic acetylcholine receptor M1 GPCR ANTAGONIST Ki 9.64 WOMBAT-PK CHEMBL
Muscarinic acetylcholine receptor M5 GPCR ANTAGONIST Ki 8.55 WOMBAT-PK
Muscarinic acetylcholine receptor M4 GPCR ANTAGONIST Ki 8.96 WOMBAT-PK
Muscarinic acetylcholine receptor M3 GPCR ANTAGONIST Ki 8.96 WOMBAT-PK
Muscarinic acetylcholine receptor M2 GPCR ANTAGONIST Ki 8.85 WOMBAT-PK
Alpha-2A adrenergic receptor GPCR Ki 6.69 DRUG MATRIX
Sigma non-opioid intracellular receptor 1 Membrane receptor Ki 7.23 DRUG MATRIX
Sodium-dependent noradrenaline transporter Transporter Ki 5.86 DRUG MATRIX
5-hydroxytryptamine receptor 2A GPCR Ki 8.16 DRUG MATRIX
5-hydroxytryptamine receptor 2B GPCR Ki 6.90 DRUG MATRIX
5-hydroxytryptamine receptor 2C GPCR Ki 7.49 DRUG MATRIX
5-hydroxytryptamine receptor 6 GPCR Ki 5.89 DRUG MATRIX
Alpha-2B adrenergic receptor GPCR Ki 7.52 DRUG MATRIX
D(3) dopamine receptor GPCR Ki 6.65 DRUG MATRIX
Histamine H2 receptor GPCR Ki 5.93 DRUG MATRIX
Alpha-2C adrenergic receptor GPCR Ki 7.24 DRUG MATRIX
Alpha-1D adrenergic receptor GPCR Ki 7.59 DRUG MATRIX
Sodium-dependent serotonin transporter Transporter IC50 4.62 CHEMBL
Histamine H1 receptor GPCR Ki 8.96 WOMBAT-PK
Sodium-dependent dopamine transporter Transporter Kd 7.25 WOMBAT-PK
Sodium-dependent neutral amino acid transporter B(0)AT1 Unclassified INHIBITOR IC50 4.36 IUPHAR
Alpha-1B adrenergic receptor GPCR Ki 7.39 DRUG MATRIX
Membrane-associated progesterone receptor component 1 Membrane receptor Ki 6.95 DRUG MATRIX
Sodium-dependent serotonin transporter Transporter Ki 5.29 CHEMBL
Sodium-dependent dopamine transporter Transporter Ki 6.93 CHEMBL
Muscarinic acetylcholine receptor M1 GPCR Ki 9.23 CHEMBL
Muscarinic acetylcholine receptor M2 GPCR Ki 8.59 CHEMBL
Alpha-1A adrenergic receptor GPCR IC50 6.85 CHEMBL

External reference:

IDSource
1NHL2J4X8K UNII
D00778 KEGG_DRUG
132-17-2 SECONDARY_CAS_RN
4017824 VANDF
4019630 VANDF
C0005098 UMLSCUI
CHEBI:3048 CHEBI
CXQ PDB_CHEM_ID
CHEMBL1201203 ChEMBL_ID
CHEMBL1200383 ChEMBL_ID
DB00245 DRUGBANK_ID
D001590 MESH_DESCRIPTOR_UI
292 INN_ID
1201549 PUBCHEM_CID
7601 IUPHAR_LIGAND_ID
1424 RXNORM
3130 MMSL
4264 MMSL
563 MMSL
d00175 MMSL
001647 NDDF
004667 NDDF
29527005 SNOMEDCT_US
372846002 SNOMEDCT_US
77390008 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Benztropine Mesylate HUMAN PRESCRIPTION DRUG LABEL 1 0143-9729 INJECTION 1 mg INTRAMUSCULAR ANDA 14 sections
Benztropine Mesylate HUMAN PRESCRIPTION DRUG LABEL 1 0603-2437 TABLET 0.50 mg ORAL ANDA 16 sections
Benztropine Mesylate HUMAN PRESCRIPTION DRUG LABEL 1 0603-2438 TABLET 1 mg ORAL ANDA 16 sections
Benztropine Mesylate HUMAN PRESCRIPTION DRUG LABEL 1 0603-2439 TABLET 2 mg ORAL ANDA 16 sections
Benztropine Mesylate HUMAN PRESCRIPTION DRUG LABEL 1 0615-8210 TABLET 0.50 mg ORAL ANDA 16 sections
Benztropine Mesylate HUMAN PRESCRIPTION DRUG LABEL 1 0615-8211 TABLET 1 mg ORAL ANDA 16 sections
benztropine mesylate HUMAN PRESCRIPTION DRUG LABEL 1 0615-8352 TABLET 2 mg ORAL ANDA 16 sections
Benztropine Mesylate HUMAN PRESCRIPTION DRUG LABEL 1 0832-1080 TABLET 0.50 mg ORAL ANDA 15 sections
Benztropine Mesylate HUMAN PRESCRIPTION DRUG LABEL 1 0832-1081 TABLET 1 mg ORAL ANDA 15 sections
Benztropine Mesylate HUMAN PRESCRIPTION DRUG LABEL 1 0832-1082 TABLET 2 mg ORAL ANDA 15 sections
Benztropine Mesylate HUMAN PRESCRIPTION DRUG LABEL 1 0904-6788 TABLET 0.50 mg ORAL ANDA 16 sections
Benztropine Mesylate HUMAN PRESCRIPTION DRUG LABEL 1 0904-6789 TABLET 2 mg ORAL ANDA 16 sections
Benztropine Mesylate HUMAN PRESCRIPTION DRUG LABEL 1 0904-6790 TABLET 1 mg ORAL ANDA 16 sections
Benztropine Mesylate HUMAN PRESCRIPTION DRUG LABEL 1 10135-606 TABLET 0.50 mg ORAL ANDA 15 sections
Benztropine Mesylate HUMAN PRESCRIPTION DRUG LABEL 1 10135-607 TABLET 1 mg ORAL ANDA 15 sections
Benztropine Mesylate HUMAN PRESCRIPTION DRUG LABEL 1 10135-608 TABLET 2 mg ORAL ANDA 15 sections
benztropine mesylate HUMAN PRESCRIPTION DRUG LABEL 1 10858-011 INJECTION 1 mg INTRAMUSCULAR ANDA 1 sections
Benztropine Mesylate Injection, USP HUMAN PRESCRIPTION DRUG LABEL 1 14789-300 INJECTION 1 mg PARENTERAL ANDA 11 sections
Benztropine Mesylate HUMAN PRESCRIPTION DRUG LABEL 1 17478-012 INJECTION 1 mg INTRAVENOUS NDA authorized generic 16 sections
BENZTROPINE MESYLATE HUMAN PRESCRIPTION DRUG LABEL 1 21695-286 TABLET 2 mg ORAL ANDA 15 sections
Benztropine Mesylate HUMAN PRESCRIPTION DRUG LABEL 1 31722-218 TABLET 0.50 mg ORAL ANDA 16 sections
Benztropine Mesylate HUMAN PRESCRIPTION DRUG LABEL 1 31722-219 TABLET 1 mg ORAL ANDA 16 sections
Benztropine Mesylate HUMAN PRESCRIPTION DRUG LABEL 1 31722-220 TABLET 2 mg ORAL ANDA 16 sections
Benztropine Mesylate HUMAN PRESCRIPTION DRUG LABEL 1 43353-580 TABLET 1 mg ORAL ANDA 16 sections
Benztropine Mesylate HUMAN PRESCRIPTION DRUG LABEL 1 43353-707 TABLET 0.50 mg ORAL ANDA 16 sections
Benztropine Mesylate HUMAN PRESCRIPTION DRUG LABEL 1 43353-796 TABLET 1 mg ORAL ANDA 16 sections
Benztropine Mesylate HUMAN PRESCRIPTION DRUG LABEL 1 43353-913 TABLET 0.50 mg ORAL ANDA 16 sections
Benztropine Mesylate HUMAN PRESCRIPTION DRUG LABEL 1 50090-3116 TABLET 1 mg ORAL ANDA 15 sections
BENZTROPINE MESYLATE HUMAN PRESCRIPTION DRUG LABEL 1 50090-3882 TABLET 2 mg ORAL ANDA 13 sections
BENZTROPINE MESYLATE HUMAN PRESCRIPTION DRUG LABEL 1 50090-3883 TABLET 2 mg ORAL ANDA 13 sections